


Pick Your Pain

by CristalDestiel



Category: Supernatural
Genre: Anal Sex, Angst, BDSM, Bondage, Dean - Freeform, Depression, Destiel - Freeform, Devil, Discipline, Dom!Cas, Explicit Sexual Content, Ficlet, Graphic, Homophobic Language, Implied Torture, Light Masochism, M/M, Male Homosexuality, One Shot, Oral Sex, Sexual Abuse, Sexual Slavery, Sub!Dean, Violence, Winchester - Freeform, Wings, angel - Freeform, castiel - Freeform
Language: English
Status: Completed
Published: 2013-06-30
Updated: 2013-06-30
Packaged: 2017-12-16 15:03:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,255
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/863366
Author URL: https://archiveofourown.org/users/CristalDestiel/pseuds/CristalDestiel
Summary: <blockquote class="userstuff">
              <p>Dean Winchester is severely depressed after losing his little brother Sam. He accidentally runs into a BDSM club while wandering the streets alone. Without knowing what he's getting himself into, he walks in and ends up having a night he won't soon forget.</p>
            </blockquote>





	Pick Your Pain

**Author's Note:**

> I will just go ahead and say this right now. This fan fiction is extremely graphic. If you are not comfortable with anything related to the BDSM world, i would suggest you turn away right now. If you are, i hope you enjoy reading this as much as i enjoyed writing it. 
> 
> PS: This fic is not beta'd so please forgive any mistakes

Pick Your Pain 

 

Dean Winchester felt dead inside. Ever since he lost his brother to the devil, he's been trying to drink himself to death. But his body had gotten used to the alcohol and even when he drank copious amounts he still couldn't numb the pain that weighed his heart down.  
  
The pain was unbearable tonight, Dean couldn't stay in. He left his cheap motel room and went wandering off into the night. He didn't know exactly where he was going, it didn't matter; he just had to keep his feet moving. He had been walking for a while when something caught the corner of his eye. There was no one around and the street was pitch dark, he stopped walking and read the sign that had caught his attention. It said "Hell" in big bright red neon lights. He automatically flinched and put his hand to his chest. "Sammy", he thought.  
  
It was irrational, and he knew, but somewhere in the deep of Dean's mind he thought going there would somehow make him feel closer to Sammy. So his feet started moving towards the sign before he could really think about much else. As he got closer he could see there was something else written on the sign. It was under the word "hell" in the same neon red light and it read, "Come exorcise your demons". Dean had years of Demons to exorcise, so he walked in.  
  
The first thing that hit him were the scents, he could smell so many different things. Candles, Sweat, sulfur, sex, lotions, leather, rubber, and every single scent hitting his nose at once, he felt dizzy but he liked it. Dizzy was good, dizzy was numbing. He could barely see anything; there wasn't a lot of light except for a couple of small candles stuck to the walls. Fire was the main form of light and Dean could understand why. He could hear faint sounds in the distance, they weren't pretty but Dean didn't care.  
  
As he was standing there taking in his surroundings, he felt a hand on his shoulder. It was a huge guy; he looked like a security guard. "What can we get you today princess?" Dean frowned at the nickname. Dean looked the guy dead in the eye and said, "I’m interested in whatever is happening in there." Dean pointed to the long hallway that stretched out in front of him.  
  
The huge guy looked Dean up and down. "You sure princess? You don't look the type."  
Dean stared at him for a minute, and then said, "I'm sure." "Alright then, suit yourself, it's 30 dollars for the first hour and then 15 for every other hour after that." Dean dug into his pocket and pulled out a bunch of crumpled up hundred dollar bills. "Whoa, whoa, someone's talking business here. Chill out, you pay when you're done." Dean stuck the money back into his pocket and stared at the hall in front of him.  
  
The big guy started leading the way and Dean followed. The hallway wasn't just big, it was huge and it went around and around, it seemed never ending. There were doors on both sides and the sounds escaping the doors were not pleasant. The guy must have seen Dean looking around because he started explaining: "Every door is called a chamber and when you are inside you can be whoever or whatever you want to be. Do you know about safe wording? My name is Gus by the way." Dean looked at him with a blank expression. But before Gus could start explaining they came to a stop. "We're here." They stopped in front of a door that had angel wings drawn on them. Dean frowned.  
  
"Angel wings in hell? Really?" Dean chuckled with no humor. "Don't be so fast to judge, the wings are just Castiel's thing but I promise you he is no angel. Go in and tell him it's your first, he'll explain all the rules to you."  
  
Dean wasn't nervous, he had no idea what he was walking into and yet he didn't care. He opened the door slowly and went in. This chamber smelled mostly of leather and wasn't making him as dizzy as all the different scents outside. There was a dark haired man with his back turned to him. He was wearing white pants and there were small black wings coming out from his back. He was organizing some stuff Dean had never seen before on a table in the corner of the room. Dean shut the door behind him.  
  
"Welcome to the chamber of the angel!" Dean stared, wide-eyed. Holly fuck, that voice! There was such much power in that voice, it was so cold and commanding. Dean wasn't scared, he didn't care, but all of a sudden his heart started pounding in his chest. "Are you prepared to do everything I tell you to without hesitation?" His back was still towards Dean and Dean still hadn't moved from the door. "Y-yes" Dean answered. "I felt hesitation, and I don't like hesitation." And that's when he turned around looking Dean dead in the eye.  
  
Dean couldn't move, he couldn't breathe. The angel's eyes were bluer then the sky and all he could do was stare. "Oh, I see, a newbie." He said, voice emotionless, turning his back to Dean again. "In here you are mine to do with as I please. You will obey every single command I give you without hesitation. You will not look me straight in the eyes unless you are told to. You are to call me sir every time you refer to me. You will not talk unless talked to. If you feel anything I do is unbearable or will leave a permanent mark you may safe word. Red is stop right away. Yellow is it hurts but I can handle it. You are not to safe word unless the pain is absolutely unbearable. Do you understand?" He said all this in a command voice that would make someone shit his or her pants. But Dean wasn't a normal someone, Dean was broken and gave no shit to what happened to him. In fact, he wanted the pain.  
  
Castiel's back was still to Dean. Dean stared at those feathers; they looked so soft, he got the urge to touch them. "I understand", Dean answered. "You understand, what?" Castiel asked, turning to face Dean now. "Everything you just said", Dean answered. Castiel chuckled, a cold laugh. "I understand SIR!" Castiel said, emphasizing the word sir. "I understand sir", Dean repeated, and Castiel got to business.  
  
"Take your clothes off and kneel over there." Castiel pointed to a circle in the middle of the room where some chains were hanging from the ceiling. Dean did as he was told without saying a word. Castiel walked over and positioned Dean the way he wanted him. "You are to always keep your head down and your knees apart to allow me full entrance." "Yes sir", Dean said keeping his head down.  
  
Castiel put a leather collar around Dean's neck and clipped the chains on him. Then he started chaining Dean's arms. "Are you a virgin?" Castiel asked. "Of course not!” Dean answered exasperated, what kind of question was that? Castiel shook his head impatiently. "Are you a butt virgin?" Dean looked up at him now, eyes wide. "Have you ever had another man's cock in your ass?" Castiel asked again as if to explain the question. "N-no" "It's 'NO SIR' and why are you looking at me? Every time you disobey me you will get punished. Castiel had a stick in his hand with strips of leather coming out of one end. He hit the stick to the floor and it made a very unpleasant whipping sound. "A virgin then, okay." Castiel put his mouth close to Dean's ear and without touching whispered "get ready for the best butt fuck of your life!" Dean got chills in places he didn't even know he had hair. He had thought this was a torture chamber, he didn't know it was a sex torture chamber.  
  
Castiel pulled the chains up and Dean felt his body being raised. He had his feet on the floor but his hands were chained above his head. Castiel stood in front of him as if studying his body. "Wow, we are going to have so much fun today." Castiel looked at Dean's cock and Dean sucked in a breath of air. Castiel walked around Dean and stood behind him. It made Dean nervous not to know what was going on back there. All of a sudden Dean felt a sharp pain; he winced. It felt like his ass was burning and then came a tingling sensation. He didn't enjoy it and he didn't hate it, it served its numbing purposes.  
  
Before he had time to process the pain, he got hit again. He inhaled sharply. He didn't even have time to feel the tingling sensation because another hit came and then another. It felt like his ass was on fire and he took it all in silence. He kept his head down the whole time just like Castiel had told him to. "Look at you taking it all in so quietly. Is the pain not enough for you?" Castiel whipped him harder getting a small wince of pain from Dean. "Now that's what I like to hear, that's beautiful." Castiel kept whipping him harder and faster until Dean's ass was completely red. It hurt and stung like a motherfucker but Dean was trying to stay as quiet as possible. Castiel whipped Dean's back and since Dean wasn't expecting the blow he winced loudly. He kept whipping Dean's back until it was red and bruised.  
  
"You are a tough one!" Castiel said, rubbing baby oil on Dean's ass. "But we are just getting started, we'll see how tough you really are. Castiel hit Dean's ass with an open palm and Dean made a whimpering sound. Castiel hit his ass again and he whimpered again. Castiel slapped his ass harder and Dean screamed out loud for the first time. "There's that voice", Castiel said while rubbing one finger in between Dean's butt cheeks.  
  
Dean's dick was getting hard, and he didn't know why. This wasn't the kind of scenario he would imagine himself getting hard in. But his body was reacting to it and he would let it. Castiel went over to the side table and Dean raised his head a little to look at those soft feathers on his back. When Castiel turned around he saw Dean had his head raised. "Oh no, that won't do. Did I tell you that you could raise your head?" "No sir." Dean answered putting his head back down immediately. You've been a bad bad boy and we punish bad boys here in the angel chamber.  
  
Castiel walked over to Dean. "Stand up straight, but don't look at me, I want you to turn your head to the right." Dean did as told. Castiel had in his hands something that, to Dean, looked like paper clips. Castiel took Dean's nipple is his finger and massaged it, then he clipped it with the nipple clamp. He did the same thing with the other one. It hurt a little, but it was a good hurt. Dean was looking to the right the entire time. "Good boy", Castiel praised him and put one hand under Dean's chin turning his head towards his own and kissing him, hard. Castiel's kiss was rough and at first Dean was surprised, he wasn't expecting to be kissed in this situation. But it was a good kiss and when he started to get into it Castiel pulled away at once, leaving him wanting more. His dick got harder.  
  
Castiel saw Dean's hard on and smiled a cocky smile. "Already? I knew when I looked at you that you were the kind that sucked on cock." "I don't suck cock!” Dean replied in an impulse, raising his head. Castiel stood still, looking at him, face completely serious. "Fuck...” Dean whispered as he quickly put his head back down. Castiel smirked when Dean wasn't watching. He walked over to the lever that controlled the chains and brought it low enough so that Dean was kneeling on the floor. Castiel took his pants off leaving the wings on his back. He had no underwear on and his dick was hard. He walked over to where Dean was kneeling on the floor and raised his head. "Look at me", he commanded. "You are gonna suck me off until I come and then you are gonna let me come all over your mouth and you are going to enjoy the fuck out of it. Do you understand me?"  
  
Dean swallowed his own saliva. "Yes sir, I understand you." "Good, now make me come!" Dean had both knees on the floor and his mouth was in the exact height it needed to be. He took Castiel's cock in his hand, feeling weird. He never thought he would suck another guy off. But he had nothing else to loose and this was distracting him from the pain, it was working.  
  
He took Castiel's cock and put it in his mouth awkwardly, not knowing exactly what to do. He started sucking on it, making swirly movements with his tongue. Castiel moaned. Dean felt good, he liked the feeling he was getting from making the guy who was dominating him this whole time, surrender to his touch for once. Castiel was pulling Dean's hair way too hard. Dean knew it was to hurt him and it did hurt, but he didn't care. He could pull all he wanted, Dean was still the one giving the pleasure. Dean was sucking, slurping, and working his way around Castiel's cock when he felt the blow. Castiel pulled his cock out of Dean's mouth and slapped him on the face in one swift movement. Dean's eyes watered. "I bet you were feeling really powerful right now weren’t you?" Castiel was stroking his cock fast; he was going to come. "Open your mouth you little whore!" Dean's eyes were still watering and he felt angry like he wanted to punch something. But he opened his mouth anyway and Castiel came all over his face.  
  
Castiel wiped his cum from Dean's face with two fingers and stuck those two fingers in Dean's mouth. “Taste me you little whore, tell me how much you like my cum! Tell me!" Castiel ordered. He was sticking his fingers down Dean's throat and Dean was gagging, eyes watering. Castiel took his fingers out and slapped Dean's face again making Dean whimper. He kneeled down to Dean's height imitating his pose. He held Dean's head with both hands and kissed him, softly as if to make it all go away. Dean kissed back enjoying the kiss while it lasted, anger evaporating. Dean was so hard, he needed to touch himself or else he would explode. He started whimpering while they where kissing and thrusting his pelvis trying to make his cock touch some part of Castiel, any part; He needed to be touched.  
  
Castiel unlocked the chains and was holding the one that was still on Dean’s collar, leading him to the other side of the room as if he was a dog on a leash. "Lay down right here", Castiel said tapping lightly. It was like a leather bed but it had restrains on the top and bottom. Dean knew he would be tied up again. While Castiel was restraining his feet, he touched his dick briefly to try to get some release, but it wasn't enough. He had his hands tied at the top of the board and his feet tied at the bottom. He couldn't move even if he tried very hard. The things keeping him in place looked like leather belt buckles.  
  
Castiel took the nipple clamps out and swirled his tongue around each of Dean's nipples very slowly. The speed in which he was doing it was driving Dean mad. Dean was thrusting his pelvis up and down. His dick was rock solid and Castiel held on to it. Dean kept moving his hips trying to make Castiel's hands move but it was pointless, he was too tied up to get any results. Castiel was holding Dean's dick in place without moving his hands, he took his indicator finger and made painfully slow movements around the slit, it was dripping wet. Castiel bent down to kiss Dean, but it wasn't a slow kiss. It was rough; he was sticking his tongue in and out of Dean's mouth as if he was fucking Dean's mouth with his tongue. "Please fuck me sir!" Dean whispered, desperately. "No" Castiel answered, and kept mouth-fucking Dean.  
  
Castiel was hard again and started touching himself, forcing Dean to watch. He was making really loud moaning noises as if that was the most pleasure he ever felt in his life. He started moaning louder, faster, gasping and Dean watching; he thought he would go insane. Castiel made himself come, screaming in pleasure really loudly to provoke Dean. There was cum dripping all over Dean's cock. "Sir, please touch me, I’m begging you!" Castiel looked at Dean as if he was pensive for a moment then said "No." Dean made a whimpering sound, he wasn't sure how much more of this he could take.  
  
Castiel spread Dean's leg out wide. "There you are, that little virgin beauty." He gripped Dean's cock at the base and swiped his hand up collecting all the dripping cum. Dean yelled, "fuck!" And thrust his hips up and down. Castiel took the cum he collected and with two fingers spread it on Dean's asshole, lubricating it. He was sliding his finger slowly around Dean's asshole, and then he played with Dean's balls a little bit. "Just fucking fuck me god dammit!" Dean yelled, in pain. Castiel walked over to look at Dean. He slapped Dean in the face. "Bad boy, you don't yell at your master. Castiel said and slapped him again. There were tears in Dean’s eyes. "Please kiss me sir, or fuck me, or just touch me, please sir, please?" Dean was begging.  
  
Castiel smiled at that. He started stroking Dean's cock very lightly. Dean started to move up and down to get his release fast. As soon as he started to move, Castiel stopped touching him. "If you move, I stop. Those are the rules." "Yes sir" Dean answered. Castiel started massaging Dean's asshole again and Dean was trying not to thrust his hips with every touch. Castiel stuck one finger in slowly and Dean winced in pain and pleasure. With every thrust of his finger inside Dean, Castiel would stroke Dean's dick. Dean thought he was going to die from pleasure. All of a sudden Castiel pulled out and let go of his dick and started mouth fucking him again. Dean was desperate, he tried to get the most of Castiel's tongue every time it entered his mouth, but it wouldn't stay there long enough. He wanted to suck on it, bite it, and release all the emotions he was feeling.  
  
Castiel licked Dean's nipples briefly and then worked his was down to his cock. He held his cock in one hand and started sucking on it, hard this time. Instead of giving Dean pleasure, he was making Dean even hornier. Dean felt like if he didn't come now the whole world around him would collapse. Castiel could feel Dean's dick pulsing in his mouth. He knew how much pain and pleasure and need he was in. He enjoyed that thought way too much. He stopped sucking on Dean's cock and went back to tongue fuck his mouth. He kept going back and fourth. Cock, mouth, cock, mouth. Dean would scream every time Castiel would stop sucking on his cock.  
  
Castiel undid the buckles that were holding Dean in place and bent him over on another flat surface. "Do you want this?" Castiel said pulling Dean's hair and turning his head over so he would look at him. "Tell me want my cock inside of you, you little whore, say it! Castiel was screaming his commands. "Please fuck me sir, fuck me hard, I want you inside of me, all of you! Dean responded. Castiel licked his middle finger and stuck it inside Dean's asshole all at once and deep. Dean screamed, "FUCK!" "Take it like a man you little faggot!" Castiel was screaming at him while Dean screamed louder as Castiel went deeper and deeper. "You like having your ass fucked by a man, don't you? You little whore. You're my little whore, and you're gonna come for me only when I tell you that you can" Castiel kept saying, as he fucked Dean deeper. "Fuck! Ah! Shit!" Dean was screaming.  
  
Castiel pulled Dean by the hair and made him stand against a wall. "Open your legs wide for me now, wider, that's it." Dean was doing as he was told; right now he wanted nothing more than to be fucked by this devil angel. Castiel held Dean's head down with one hand, with the other he was stroking Dean's cock lightly, and all at once he stuck his cock inside Dean's asshole without a warning. "Ahhh! Mother Fucker!" Dean screamed. "Are you gonna be a little pussy? Or are you gonna take my cock in your ass like a man?" Castiel was fucking Dean's ass, masturbating him and saying dirty things in his ear at the same time. Dean didn't know this kind of pleasure was possible. He forgot anything outside existed and even though it hurt like a son of a bitch, he liked it. After months of wandering around lost and broken he felt whole now, at least in this moment, with this angel's cock inside of him, he felt complete.  
  
Castiel kept thrusting and masturbating and Dean was about to come. "Do not come yet! You will only come when I say you can, do you understand me?" "Yes, sir." Dean answered almost in tears because he had been holding his cum for so long. When Castiel was about to come himself, he whispered in Dean's ear: "Come for me, come for me now." It was an order. Dean let it all out; the longest orgasm Dean had ever had in his life. He didn't know he had that much cum inside of him. The wall he was standing against had a huge white spot on it, all of it was his cum. Castiel came at the exact same time and Dean felt it all inside of him. It was the most pleasure he had ever felt during sex in his entire life.  
  
Castiel nibbled Dean's ear and held him for a second. Then he threw him on the wall and kissed him. But really kissed him this time. Not too soft, not too rough, not provocative. A real kiss, if Dean didn't know any better he would have confused it for a passionate kiss. They kissed for a long time, and this time when Dean joined in, Castiel didn't move away or hit his face. Now Castiel was stroking his face, very lightly, almost lovingly. Then Castiel pulled away slowly and looked into Dean's eyes and let Dean look into his.

 "You're broken inside, that's why you came to me today." "How do y-" Dean began. "Shhh, let me finish" Castiel said, putting his finger to Dean's lips gently. "I know you're broken and I don't know why, but sometimes you have to take something that is broken and break it in other ways, that’s the only way you can really appreciate the parts that are unbroken." Dean was confused and Castiel could tell so he kept talking. "Did you see how many things you felt in here today? You are still capable of feeling things; it's all inside of you. You just have to dig deep and you will find them.” “How did you know I was broken?” “I beat you harder than I have ever beaten anyone and you barely made a sound. Only someone who is feeling a greater pain inside can ignore or welcome physical pain like you did.

What this angel was saying made total sense. But why would he say these things to Dean? Why now? Wasn't he supposed to be this big bad torturer? Castiel turned away from Dean and started putting his clothes on. "Go pay Gus at the front, and I take tips." Castiel said, voice completely different than it had been a second ago; it was cold and commanding again. Dean put his clothes on and left a 200 dollar tip on the table. He was about to walk out when he stopped in his tracks and turned around. The angel was in the exact same position he had been when Dean came in: his back to Dean, white pants, organizing the sex toys. He ran up to Castiel and pushed him against the wall, kissing him again. Castiel was a little taken aback but he kissed back. Dean finally got the courage to touch those black wings. They were just as soft as he had imagined. Dean stopped the kiss, looked Castiel in the eye and said: "You know, you really have to decide, angel or demon?" Then Dean walked away planning on returning very soon.

 

**Author's Note:**

> Hope you enjoyed that :) 
> 
> Please leave Comments and Kudos, but let's be nice okay? This is one of my firsts, i'm still not an expert at this. But it's practicing that you get better right! So i will accept constructive criticism. Thank you for taking an interest in reading this fan fiction.


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